Potassium Carbonate → 1'-[6-(3-Methyl-1,2,4-thiadiazol-5-yl)pyridazin-3-yl]-2,3-dihydrospiro[indene-1,4'-piperidine]

HRID 2036071ノート

反応式

HRID 2036071 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.Cl.[NH:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:15]3[CH2:20][CH2:19][C:18]4([C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[CH2:17][CH2:16]3)=[CH:7][CH:6]=2)[S:12][N:11]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 109218293-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazineHCID 225093272,3-Dihydrospiro[indene-1,4'-piperidine] hydrochloride

生成物 1

HCID 866399981'-[6-(3-Methyl-1,2,4-thiadiazol-5-yl)pyridazin-3-yl]-2,3-dihydrospiro[indene-1,4'-piperidine]収率 60.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

3-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazine (51 mg), 2,3-dihydrospiro[indene-1,4′-piperidine] hydrochloride (78 mg) and potassium carbonate (70 mg) were suspended in N,N-dimethylformamide (3 mL), and the suspension was stirred at 80° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed twice with aqueous sodium hydrogen carbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane to 50% ethyl acetate/hexane) and recrystallized from hexane/ethyl acetate to give the object product (53 mg, 60%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed twice with aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane to 50% ethyl acetate/hexane)
  6. customrecrystallized from hexane/ethyl acetate

出典と根拠

ORDレコード
ord-4e0355b16b984d69b678132c3e425198
出典データセット
uspto-grants-2013_11
特許番号
US08575167B2

反応ノート

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